


Cherry-gold lips

by cherrygoldlove



Category: Teen Wolf (TV)
Genre: Blow Jobs, Businessman Derek, M/M, Medical Examination, Overstimulation, Prostitute Stiles Stilinski, Unsafe Sex, slight non-con, speculum used on a male
Language: English
Status: Completed
Published: 2015-02-11
Updated: 2015-02-26
Packaged: 2018-03-11 21:26:56
Rating: Mature
Warnings: Rape/Non-Con, Underage
Chapters: 2
Words: 4,690
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3333476
Author URL: https://archiveofourown.org/users/cherrygoldlove/pseuds/cherrygoldlove
Summary: <blockquote class="userstuff">
              <p>Blow it and it's golden.</p>
            </blockquote>





	1. Chapter 1

The black limousine slowly rolled through the street carefully observed by multiple sets of hungry eyes.

This district wasn't frequented by the wealthy and powerful, it was a place for the desperate and the lonely. Women and men, all scantily clad were standing in every doorway, shivering in the cold, early autumn air, the wind carrying the promise of a soon rainfall. The car finally came to a slow stop near an entrance to a dark and narrow alley, the tinted window lowering slowly uncovering a handsome, scruffy face of a guy in his mid-thirties.

"Hey you, Red Hood, show yourself" The man, Derek, said in the direction of a lanky boy huddled near to the alley. The boy wore blue jeans that looked two sizes too small but still managed to hang from the thin hips and a red, faded long-sleeved shirt with a hood, his face in the shadow. He was almost plastered to the concrete wall, trying to hide from the bitter wind and maintain as much body heat as possible, but upon hearing the call, he quickly pushed away from the wall and made couple of steps towards the limo and into the rays of a nearby street lamp. Trembling hands reached up to lower the hood. The man in the car grunted with appreciation at seeing the high cheekbones, little, upturned nose and wide lips, the boys skin milky white but splattered with a myriad of little freckles.

"You'll do" he grunted. The driver got out and opened the door from the other side of the car, indicating the boy to get in.

Once inside, Derek directed his young guest to sit on the opposite side. He then reached for his phone, concentrating all his attention on the little screen while typing. That's what you got from having your own business - no free time.

They drove through the night covered city, far away from the poor quarters. The young prostitute still shivering, despite the interior being pleasantly warm. Moving his hand up and down his arms to try and warm himself up.

"Stop fidgeting." He chastised harshly, for the first time tearing his gaze from the telephone and looking at his passenger. After a moment of consideration, he threw him his overcoat. "Cover yourself" he ordered gruffly, eyes returning to his previous task.

Stiles bundled up in the coat, settling in one corner of the car, watching Derek with wary eyes. Soon they arrived at a hotel. The car coming to a stop in front of the main entrance. He buzzed the glass partition separating him from the driver down startling the almost dozing boy.

"Boyd, Take him by the back entrance"

"Yes, sir"

Derek got out of the car, leaving the slightly scared teenager inside.

 

***

 

 

He hears the front door opening when he's pouring himself whiskey from the side table. He discarded his jacket and tie, unbuttoning the first couple buttons of his crisp white shirt, towed off his shoes.

He turns around to face his guest when he hears a quiet voice almost whispering. "Sir?"

"Good, you're here. Undress"

The teen fidgets, looking around.

"I'd... I need a bathroom. To get ready." he stutters. Then adds. "Sir."

Derek looks at him, making his way to the leather sofa and sitting down.

"I won't fuck you tonight, just your mouth. Strip." He demands and takes a sip from the crystal glass.

Reluctantly, the boy reaches to the hem of his shirt, pulling it up and exposing slim, almost too thin stomach and torso. After towing off his shoes, he unbuckles his trousers, pulling them down. He's not wearing anything underneath them. He straightens up, this arms crossing in front of his body, trying to hug himself, maybe shield a little from Derek's gaze.

"Come here, kneel" Derek admires the slim youth and then motions for him to come and sit between his spread legs. When the teen obeys, he continues. "Take my dick out." He's already hard, twitching, when the boy finally pulls it out. "And now suck me, no hands." he demands.

"C-condom, sir?"

"No condom and I'll come in your mouth." Derek declines. "Take it or leave it"

He knows the little whore can't say no and he's proven right when the boy ducks his head for a moment and then leans in, mouth open.

He begins with a gentle suck, tongue moving on the slit and then sliding under the head, lips spreading wider. The boy is marvelous at his job, working the dick like a pro.

Derek gives a low rumble of satisfaction, burying his free hand in the young man's short hair - not quite a caress, not quite a demand, but the hustler is fast on the uptake, deepthroating it all in one go, holding there until tears gathered in the corners of his eyes. Derek gives a short, sharp jab watching those tears fall down peach-pink cheeks. The boy is a work of art, even if a little malnourished and weary. Derek is enthralled by his cherry-gold lips stretched so obscenely around his cock, by the big chestnut eyes surrounded by tear-stained, long, dark lashes, honey-colored moles scattered upon his skin making it look even paler that it was. He'd paint him if he could. He held the boy's hair tighter, holding him in place as he fucked his mouth, chocking him a little. But the teen sat there unmoving, not running away, not struggling, the only sign of defiance were his now tightly shut eyes. Derek thought the boy must have learned his lesson sometime in the past as he came hard and hot in the lush mouth.

He let go of the youth's hair, bringing his fingers underneath the boy's chin, lifting it up, admiring, then took the whiskey glass to his lips draining it all, eyes never leaving the hot, chocolate gaze.

He put the glass back on the couch and let go of the rosy, fucked out face, using both hands to tuck himself in.

Derek reached to his pants front pocket, retrieving folded in half bills putting them in front of the boy’s face. He tutted with disapproval when it seemed the youth wanted to reach for them with his hand. He didn't have to wait long for understanding to light up in the deep, brown eyes and for the boy to lean forward again, opening his mouth and gently taking the folded dollars in his teeth.

"Good boy." Derek murmured. "You can go now."

He watched amused as the teenager got up to his feet and went back to the place where he left his clothes, bending down to retrieve them, unconsciously giving Derek a teasing look of his plump behind.

Skinny arms gathered up the clothes, bundled them up and pressed against the scrawny body, trying to hide his half erect penis. _Cute_ , Derek thought, _Interesting and cute_. The youth, now weirdly embarrassed with his naked body, seemed to look around where to hide and dress again. Derek snorted, lifting a brow up as the boy's startled eyes found him again.

"Out, boy, the way you came here. Boyd will take care of you now."

The youth nodded vigorously and headed out to the corridor, the money still awkwardly held between his teeth.

Just as he watched the last glimpse of the boy's buttocks disappearing he heard the main doors to his apartment opening.

"Boyd!" He called out.

 

***

 

"What's your name, boy?" The tall, dark-skinned man that was his latest John's driver asked him, closing the apartment doors behind them.

"Stiles, sir." he replied looking up hopefully, shoving the money in his front pocket. He didn't count the bills, but knew it was a lot. The fist bill was a hundred, and the pile was pretty thick, so even if the rest was just one-dollar bills, he earned more in this hour than in the past week. Patrons didn't go for his type of skinny, it seemed. And now, he hit the jackpot without even having to get fucked. But well, if this one wanted his ass, he wasn't about to say no.

"Follow me, Stiles."

So he went, down the corridor and towards another set of doors. The man opened them passing a card over a bump in the wall. Stiles was led inside and towards the kitchen table. Kinky, but he had worse.

"Sit." the black guy told him, indicating a chair, while he himself sat on the opposite side.

 _Aaand here it goes_ , Stiles thought, _kink negotiation_.

"Mr. Hale asked me to offer you an exclusive contract. He is a very busy man and has no time to look for... entertainment, and you seemed to please him greatly this evening. He's not a cruel man and his sexual kinks are few and mild, so do not worry. Mr. Hale would like to offer you your own small suite in this building and a monthly allowance which's amount is up for discussion. In exchange you will be available to him and only him at all times. You will go through a thorough medical examination to ensure your good health and you will be given Mr. Hale's blood test results in exchange. All sexual acts will be carried out without condoms. Do you agree?"

Stiles was stunned. One good blow job and he was golden? He felt like crying. It was too good to be true. There must be something wrong with this situation, with this Mr. Hale. Good things didn't happen to Stiles just like that! The last two years were a horror he didn't want to ever think about, hopefully never. He was one step from dying from hunger and now, here he was. Being offered heaven for the measly price of being fucked daily by a handsome, rich businessman?

"Where do I sign?"


	2. Chapter 2

**Notes for the Chapter:**

> This is some porn, followed by medical porn.  
> It's not accurate, it's pure fantasy ;)  
> Thank you for your amazing and motivating comments!  
> You guys are awesome! <3

*Two months later*

Stiles was fighting to keep his tears at bay and losing phenomenally.

He was standing pushed against a wall, naked except for a blue-gray stripped tie pushed between his teeth, parting his lips wide and making him drool and gag as his tongue was also being forced back uncomfortably down his throat. A sharp pull on the tie making him jerk his head back again, exposing his throat to more angry, biting kisses, making him gasp and whine.

Derek was right behind him, pounding hard inside his body, one hand wrapped around his middle, not letting him get away from the sharp trust and the other hand holding the tie, bending his head back. 

Stiles whined again, the sound long, wrung out, almost painful. He knew Derek was close, that it soon would be over but… it was really becoming too much. He already came, two times really, and now he was just too much on the painful, desperate-to-get-away side of over-stimulation. His whole body trembled and he was well aware that the moment Derek would slip out of his body and let him go, he would crash to the ground, not an ounce of strength left.

The man behind his back gave two, three hard, deep jabs of his hips, pushing just that much more inside, that Stiles feared he’d get a bruise on his stomach, and then slumped against his back, the man’s hips moving slowly now, only with gentle swaying motion, almost as if to sooth his oversensitive channel, riding the last of his orgasm.

After a moment the tie was loosened and gentle hands cradled his tired body, lifting him up and carrying to an already filled bathtub, lowering him to soak in pleasantly warm water. 

Stiles’ head lolled on his shoulders, forehead coming to rest on the side of the tub. The same hands soon lifted his head and a thumb caressed the sore side of his mouth where the tie bit in, leaving angry, red welts. 

“You did good, Stiles.”

“Thank you, sir” He managed to mumble after a moment, his voice as blurry as his sight. Then his head was lowered again, resting comfortably on a fluffy, white towel, and he felt himself sink into a deep slumber, the last thing registering was a hand caressing his hair.  


*

Stiles woke up in his bed. 

The bed sheets clean and crisp and milky white as always. 

He stretched a little, feeling how sore his body still felt, the wide yawn making him wince. 

The sun was high in the sky but he didn't feel any rush or need to get up. 

Yesterday was hard, but that only meant that today would be lush and cozy. 

He stretched out again, sinking back into the soft pillows, closing his eyes again, reminiscing how he ended up a pampered little dirty secret…

*

That first night he was brought to an apartment two floors down from the man that hired him. 

The dark-skinned man, Boyd, who brought him there, told him the place would be small, but… it all depends on by whose definition. Yes, it was way smaller that the Boss’ , but by far it was the biggest Stiles ever could say he lived in. It was almost the size of his old family home…

But not going there. Never. 

The suite was all browns and beige, warm pastel colors so different to the black and grey, sleek and shiny and cold interior two floors up. 

Boyd told him to get comfortable, that he’ll find the fridge full, bathing supplies in a shelve in the bathroom and some clean clothes in the bedroom. And tomorrow, around noon he’ll be brought to a lawyer and sign up the contract, if all goes well he’ll be brought to a doctor and then shopping for basic things. 

After he was left alone, he felt lost. He never really was in such a luxurious place and he was afraid to touch anything in case he’s dirty it or worse, break. 

But hunger soon discarded him of his meekness. 

Soon he found himself pleasantly full with food, bathed and clean and lying down in the softest bed ever. He didn't even know when he fell asleep.

*

The next day was one of the most mortifying of his life. 

The meeting with the lawyer was pretty alright at first, then it got a little more embarrassing.

His name (Stiles Stilinski, he had nothing to hide, not anymore), his address (the corner of St. Luise and Franco’s, or really, any street corner) and such other necessities. Then they came to his sexual history and preferences.

They thankfully omitted the dreaded – how many partners? – but he still had to admit to his first time with anal penetration happening as a paid transaction, something that still brought him nightmares. 

Hard limits? No killing, no permanent damage or disfiguration, no starvation or food play and no fisting (Stiles learned that one the hard way, unfortunately) and no blood play and no gang bangs.  
Oh, and no scat, that’s just nasty!

To the rest he made little ad notations, things he considered soft limits when some of his needs were met (whipping? Yes, but no blood drawing and not for longer periods of time).

He would be monogamous, not search for other sexual partners besides Mr. Hale – maybe it didn't allow him to pursue any romantic interests, but damn, after the street work, he wasn't really a boyfriend material. And being an exclusive sugar baby to one man was so much better that a whore to hundreds. And he’ll be at the beck and call of Mr. Hale at every time of day and night. 

In exchange he would get all that Boyd promised on behalf of Mr. Hale that first night. Housing, money, free time. The sum he was presented with was… more than acceptable. If he could put aside even half of it, in two years, he could be a very wealthy person and go to college and…

“When does this contract terminate?”

The lawyer shuffled some papers, finding some note or the other before replying.

“The contract can be terminated by Mr. Hale at any given moment, after which you’ll be paid out a farewell fee in the sum of two months allowance and you’ll have to leave your apartment in twenty four hours. After six months from this date you will be called to my office again and will be given the chance to terminate it of your own free will or continue and revisit terms. Should you choose to end the agreement you’ll also get two month’s pay and will have to find other accommodations in the period of twenty four hours.”

After some other minor changes he finally signed the document. 

Whatever happens after that, six months are not that long…

*

He sang a different tune when, after a nurse drew his blood and collected other body fluid samples, he was handed a hefty sized dildo and told to stretch himself to accommodate it. 

He held the black monstrosity in his hands and thought that, well, despite… being well gifted by the gods Mr. Hale was not *that* big… 

No one seemed to interested in his doubts and he was swiftly guided to a secluded room with a bed and a big bottle of lube standing on the bedside table and a small chair standing in one corner.

“Take your time, there’s no rush, push this button when you’re done.”

The nurse informed him before leaving. 

He really had no idea why he was made to do this but it wasn't really his place to ask anymore. 

He sold himself for the time being and this thing he was asked to do now, it wasn't breaking his limits. 

He didn't even think to write something like this in his contract. Now he would, because it felt bizarre… 

Stiles sighed deeply, laid the dildo on the bed and proceeded to undress himself, throwing the clothes on a chair. 

He took the bottle of lube and sat and the bed, back resting on the wall, knees brought up and spread. He squeezed some cold liquid on his fingers, warmed it up a little between his digits and then brought them to his hole, rubbing around in soft circles until he felt himself relax.  
They told him not to rush, so he’ll damn well take his time to work up to this monster of a toy.

*

Ok, he didn't think it through. 

He came hard and fast after the dildo pushed against his prostate on its second glide in and he couldn't find any tissues. Also his backside was overflowing and sticky with lube. He felt like a naughty teenager after his first cumming. 

Was he supposed to clean up with the bed sheets? Leave himself dripping? Leave the dildo in or out? Should he get dressed? Should he get dressed and leave the toy inside…? 

That thought made him feel hot again, blush rising high on his cheeks. Maybe that was what Mr. Hale wanted today…?

But the nurse told him to push a button when he finished so… he was finished. 

He took the toy out, or really gave it a slight push with his muscles and it slid out with a soft, wet sound. He liked to play like this sometimes… 

His legs were still a little shaky but he managed to get to the door. Right above the button was a small board with instructions. 

The bedside table, oh, he forgot to check it when he came in. Now that he looked at it, on the lower shelf was a stack of paper towels and a medical robe. He cleaned up and put the robe on. Then he pushed the button and waited patiently for the nurse to come back. 

*

He was escorted to another room, a doctor’s office this time.

“Doctor Deaton will be right with you” 

And the nurse left him alone again. He looked around the room a little. A standard medical office as far as he could tell. A desk, two chairs, some information boards hanging around. He smiled when he saw a cartoon image of a prostate declaring that a healthy prostate made for a happy household, whatever that was supposed to mean. 

The doors opened and into the room went a man, somewhere around mid-forties, but already bald. For a moment he thought Boyd came to collect him, but this man looked much more cheerful and was wearing a white, doctor’s white coat. 

“You must be Stiles, right? I’m Doctor Allan Deaton and I’ll be performing your thorough medical exam on behalf of Mr. Hale.” He proceeded to close the doors behind himself and going deeper into the room, sitting down behind his desk and putting the papers he held in his hands on the top. 

“Would you like to sit down?”

“Um… no, not particularly…” Stiles’ flushed lightly. Maybe he wasn't in some deep discomfort but he was sure there was still some lube residue inside…

The doctor only smiled lightly at him, smirked really, and shuffled some papers, finding one and reading it in silence.

“Ok, seems your blood is clean from any STI’s, that’s good.“ He hummed lightly reading on. “And the rest looks ok, everything’s normal. Good.” He looked up at Stiles. “Let’s proceed to the exam. You may undress.” 

That was a familiar moment. He quickly untied the robe, took it off and laid it on one of the chairs.

The exam went as any he ever undergone, really.

Weight, height, check of his scalp, any blemishes on his skin. He blushed hard when the doctor asked him to caught, hand on his balls, and Stiles could hear a wet, dirty sound behind himself. The Doctor, thankfully ignored it, his touch and demeanor very clinical and professional. 

He discarded his latex gloves and went back to sit behind the desk, choosing the right piece of paper and writing things down. 

After a while he looked up at Stiles, who was still standing awkward in the middle of the room.

“You may walk behind the screen and hop on the chair, I’ll be shortly with you.”

Stiles was confused. Chair? Behind the screen? Shouldn't the exam be over and shouldn't he go back to Mr. Hale now? 

Dr. Deaton seemed to catch up to his confusion and looked at him with something close to pity. 

“I did mention a thorough examination, didn't I? Go, behind the screen there’s a stirrup chair. I’m sure you can figure it out.”

Mortified, he followed the doctor’s orders, and sure enough there was a gynecologist chair there. He always thought it was not for male patients, the doctor could easily touch his prostate with him just bending over. 

He was startled when the man appeared behind his back.

“What now? Hop on.” He admonished softly and went to wash his hands again and put a fresh pair of gloves, gesturing for Stiles to sit on the weird contraption. 

He sat gingerly, and then was guided to lay back by the doctor.

“Put your legs up, yes like this.” Dr. Deaton said as Stiles allowed himself to be moved and put in the correct position. “Feet here, in the stirrups. Good, now scoot a little way more down."

He was in many embarrassing and uncomfortable positions in the past but he rarely felt so exposed and humiliated as he was now. Half laying in a gynecologist chair, his butt almost hanging over the edge, legs wide spread and mostly immobile. His stretched open, dripping hole on display for the doctor’s… pleasure? That was the weirdest doctor-play he ever participated in. And it was still not over.

He felt gloved hands spreading his cheeks further apart. 

“Nice, candy-pink color, slightly swollen. When was your last penetration?”

Stiles gave a deep sigh, eyes firmly on the ceiling.

“A week and half ago.”

The doctor tutted disapprovingly.

“Must have been a rough one, I’ll write you some soothing gel for it.” He let go of the boy’s cheeks. “I’m going to put a finger in, please try not to tense up.” He said and did exactly that.

With the amount of preparation he got, the finger went in smooth. 

“Good, now I’ll add one more.”

Not meeting any resistance, the fingers slid in easily. The doctor turned them this and that way, twisting and scissoring.

“Now, squeeze as tight as possible and don’t let go until I tell you too.” 

So, Stiles did. Squeezing his stretched muscles as much as he could, holding tightly. His hands curled into tight fists too.

Deaton hummed approvingly, turning his fingers again and then giving a couple sharp jabs that made Stiles gasp out, almost losing his concentration and the hold he had on the doctor’s fingers.

“You can relax now, very good.” He removed his digits and turned to a side table. “You have a very good grip, good elasticity. Admirable control of the sphincter and pelvic floor muscle, really. Still, even good things can be improved. You heard of the Kegel exercise?”

“Um… no, not really.”

“It’s much similar to the exercise we just performed but instead of squeezing my fingers you’ll have a… squishy toy, that instead of emitting sound, will count your repetitions.”

Fun, Stiles though with sarcasm.

“One more thing and you’ll be free to go. You are familiar with speculums?”

“What!?” Stiles looked down, between his legs at the doctor. Oh no, no, no. He knew about this fetish, now he remembers, damn, he should have added it to the contract. NO internal play! 

“There is nothing to worry about, Stiles.” Deaton continued as if the boy didn't say a word. “You have stretched yourself out admirably, the discomfort should be minimal.” He lifted up the dreaded object to show to the terrified boy. “And I’ll lube it up more, even though you're still dripping wet.“

Upon seeing it Stiles gave a relieved sigh. 

The speculum wasn't the horse sized, metal contraption that he saw in some porn vids. It was relatively small, made from clear plastic and the blades weren't even longer or thicker than the black dildo he used earlier.

“Ok, go ahead.” 

The feeling was still far from pleasant, and the way it was opened up inside him felt way too personal – the feeling made even worse when Deaton bent down to look inside, flashing a little flashlight. 

“Rosy-pink, no lacerations or scarring. Your prostate looks good too, no worrisome swelling. I’ll exam it with my finger now, please try not to jump.” 

Ha, ha it was easier said than done. Stiles’ body contracted, clenching hard on the speculum.

“Excellent.” Deaton praised. “And we’re done. I’ll remove the speculum and leave you to get cleaned up. Once you finish please meet me at my desk.”

The object slipped out easily once the blades were closed down, and the doctor went out, back to the main part of the office.

Stiles laid there for a moment, he brought his legs up to his chest and held for a moment, relaxing his back.

After a moment he got up from the chair – or more accurately, he fell down out of it, cleaned up as much as he could with the things provided and went to meet the doctor again.

*

He got prescribed with a full array of intimate gels and lotions and creams. One to ease the light swelling the doctor observed and the rest in anticipation of the future need.  
Oh, and the toy for the Kegel exercise – Twice a week, Stiles. – Dr. Deaton advised.

He’d need one of the gels now, and was now glad of the thoughtfulness of the doctor.

Stiles reached to the bedside table’s drawer and retrieved the bottle he needed. He administrated the heavy cream to his aching rim, swirling a finer inside, wincing a little.

When he finally got out of the bed and made his way to the kitchen, he smiled softly seeing the silver tray placed on the table. He lifted the cover up and was pleased to see an array of soft, mushed foods – jams, fruit smoothies and purees, couple of his favorite vanilla milk puddings. Delicious and sure not to hurt his mouth. 

Life was good.

**Author's Note:**

> always, always use condoms!  
> and comments are love!


End file.
